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Troubleshooting: Outlook Add-in

This page provides answers to issues that users may experience with the Secure Messaging Outlook. If your issue is not resolved here, try the FAQs. If you are still having difficulties with something, please contact your portal admin or Secure Messaging support: wilson@secure-messaging.com.

Repairing a Corrupt ClickOnce Application Cache

ClickOnce is a Microsoft technology that enables the user to install and run applications and Outlook add-ins. ClickOnce applications are installed in a specific user directory. This directory, or cache, may be corrupted resulting in errors during installation such as “Value does not fall within the expected range,” etc.

Running the following command from an administrator elevated command prompt will repair the cache:

rundll32 %windir%\system32\dfshim.dll CleanOnlineAppCache

If the previous command does not resolve the issue, it may be necessary to remove the ClickOnce application store:

Using Distribution Lists

Many users that need to communicate with large groups on a regular basis rely heavily on distribution lists. The Outlook add-in does not prevent people from using distribution lists, but an extra step is required. Distribution lists must be expanded before they are compatible with the Secure Messaging Outlook add-in. Follow the instructions below to learn how to do this.

When a user adds a distribution list to the TO field (see below) it is collapsed by default. (This is evidenced by the “+” symbol next to the list title).

Click the + symbol. You may be prompted with a message like the one above.

Click OK (replacing the distribution list with the actual email addresses is exactly what we want to do).

File Attachment Progress Bar Issues

When you are downloading or uploading file attachments using Secure Messaging add-in, the progress bar will stay on top of Outlook (and all other programs) and you will not be able to move it until the action of uploading or downloading is complete. You are able to continue working with your other programs, but the screen area behind the progress bar will not be visible. Outlook will be locked in the case of uploading a file attachment.

To avoid this issue, please ask your administrator if the asynchronous file attachment feature is enabled on your Secure Messaging platform. With this feature enabled, file attachments will be uploaded and downloaded asynchronously without blocking Outlook.

Error Message: Local Information for this Message is Corrupt

For security reasons, the Outlook add-in stores some data (encrypted) locally. If you are receiving an error message telling you that your local cache is corrupt, it means that previously stored and encrypted access data and metadata have somehow become invalidated. An invalid cache can happen for a number of reasons:

If a user attempts to manually edit the local cache;

If an external application or user (malware, a hacker, a virus) attempts to modify the local cache in any way;

If the Outlook add-in is involved in a crash;

If the local cache cannot be found (it was deleted or moved).

If your local cache has been invalidated, it is easy to fix. If you select a secure message that gives you the error, and then use the add-in to retrieve the secure message again by clicking the refresh icon at the top of the Delivery Slip, the local cache will be recreated. We do not force auto-retrieval so that you can make a case-by-case decision about which secure messages you’d like to re-retrieve.

Make sure the “Secure Messaging Office Add-in” or “DeliverySlip Add-in” checkbox is selected and click OK.

Close the window and restart Outlook. The add-in should load properly.

If it does not, please repeat the above instructions for Step 4.

If the “Secure Messaging Office Add-in” or “DeliverySlip Add-in” checkbox is set back to unchecked, please contact your administrator with the following text in the subject line: “Secure MS Outlook Toolbar COM add-in won’t stay enabled – Request Advanced” and include a screenshot of the COM Add-ins dialog with the Secure Messaging Office Add-in selected.

NOTE: If none of these steps solve your problem, please contact your administrator and provide a detailed explanation of your problem. Your support case will be escalated to a Tier 2 agent who will contact you personally by email to complete Step 5 below.

5. Administrator Advanced Troubleshooting

Click Start > Run and enter regedit

Go to this folder: HKEY_CURRENT_USER\Software\Microsoft\Office\Outlook\Addins\OutlookToolbar.AddinModule

In the folder, check for a key called LoadBehavior

If you don’t have this key in the registry, it may be because the add-in was uninstalled in a previous step. Please re-install the add-in and then repeat the previous steps. Remember to close Outlook before installing and when the installation completes, please wait until you see the dialog “Secure MS Outlook Toolbar registered successfully.” If the same behavior exists, and you still do not see the registry folder (make sure to press F5 to refresh the registry editor), please proceed to step 5.1.

If you do see the LoadBehavior key, please ensure the value is 3. If it is 2 or another value, please close Outlook and set LoadBehavior value to 3.

After setting the LoadBehavior to 3, restart Outlook. If the add-in still does not load, move to 5.1.

5.1

Send all of the log files in this folder to support and wait for a response before proceeding to step 5.2.

If you do not see this file, proceed to step 5.2.

5.2

Close Outlook

Open the file addin-loader.log (above in 5.1) and copy the location path of the Startup directory (near the top).

Open a Command window (Start / Run / cmd), type cd, then a space, then paste in the folder path you copied in the the previous step. To paste in the command window, click on the black icon at the top left corner and choose Paste. Click enter.

Once the directory is changed, enter the command based on Outlook version:

If you are using Outlook 2010 64-bit, 2013 64-bit or 2016 64-bit, type: regsvr32 adxloader64.dll

If you are using Outlook 2007, 2010 32-bit, 2013 32-bit or 2016 32-bit, type: regsvr32 adxloader.dll

You should see a confirmation message that the command was successful.

Close the command window and start Outlook. It should work correctly now.

6. Ensure that your Add-in has not been disabled by Outlook:

7. Ensure Outlook is not running as Administrator:

For the standard installation of the add-in, the application is installed for the local, active Windows user only. If the user is running Outlook as an administrator, or as another user, the Secure Messaging Outlook add-in won’t be able to load. It is recommended to run Outlook as the same Windows user that installed the add-in.

8. Uninstall and reinstall the Toolbar

If none of the above steps correct your problem, please uninstall and reinstall the add-in You can do this by following the uninstall process (opens in new window). You can reinstall by signing in to the Secure Messaging webapp, clicking Install Apps > Windows > Microsoft Office Add-in and follow the instructions on this page (opens in new window) to complete the installation.

If uninstalling and reinstalling does not correct the problem, please contact your administrator.

Active X Error When Using Email Signatures

Editing Outlook signatures in the default Microsoft Work editor can result in unintended insertions of Smart-Tags, which will cause Active X errors in many situations.

The Secure Messaging Outlook add-in and the Secure Messaging webapp are not causing these errors (these errors also occur in instances when the without the Outlook add-in installed.

If you suspect your signature has Smart-Tags that are causing problems for you or your recipients, you can check easily by opening an email message with the issue and right-clicking anywhere in the message body, then selecting View Source from the menu that appears. This will open a text editor full of HTML code. You don’t need to worry about most of this, but near the end, look for a block of text that looks like this:

If you have determined that you have undesired Smart-Tags in your email signature, follow these steps to manually remove them:

If you are using Outlook 2003 on Windows XP under the default installation path, click Start > Run and enter the following path into the dialog box: C:Documents and Settings%username%Application DataMicrosoftSignatures

You should have a window open with all of your signatures present. There are three versions of each signature that you have: HTML, rich text, and text. Before you continue, you might want to make a backup of the HTML signature that you are about to edit.

Right-click on the HTML file for the signature you want to edit. Select Open With… > Notepad. Remove the text above (the text containing <o:SmartTagType>, etc.). Save the changes and close the file. Now when you send a message using this signature, you should not experience any Active X error messages.

Invalid SMTP Email Address Error

An SMTP email address is an email address in the following format: name@domain.

If you are receiving an error message regarding an invalid SMTP email address, it is because the contact that you are addressing your secure message to is not recognized as being in this format. The two most common reasons for this are that the contact is either an MS Exchange contact or a distribution list.

If the contact is an MS Exchange contact, you must obtain his or her true email address (in the SMTP format, shown above). If the contact is a distribution list, you must expand the list so that it is replaced by the actual e-mail addresses.

Outlook Connector for Hotmail Causes Issues

For security reasons, the Outlook Connector for Hotmail / Windows Live is currently not supported by the Secure Messaging Outlook add-in. The Hotmail connector is known to create problems with several add-ins for Outlook. We recommend that you disable the Hotmail Connector if used in conjunction with the Secure Messaging Outlook add-in.

Reports have also been made that the Hotmail Connector creates issues with the Outlook Calendar when used with other third-party add-ins. If you are experiencing issues with your calendar, please ensure you remove the Hotmail Connector.

IMAP Support

The IMAP protocol is currently not supported by the Secure Messaging Outlook add-in. The add-in is designed to ensure corporate security of message and file attachments; the IMAP protocol syncs message and attachment data back and forth between Outlook and the mail server in a plain text format, allowing decrypted secure messages to be sent in the clear over the internet and saved unencrypted on the mail server. This constitutes a security breach. We recommend that you do not use IMAP with the Secure Messaging Outlook add-in. Please contact your administrator for more information or alternatives.

Error: Application Cannot Be Started

If you get this error when installing or upgrading the Secure Messaging Outlook add-in, click Details to see the following information:

>ERROR SUMMARY>Below is a summary of the errors, details of these errors are listed later in the log.>* Activation of C:…Secure MS Outlook Toolbar.appref-ms| resulted in exception. Following failure messages were detected:>+ The referenced assembly is not installed on your system. (Exception from HRESULT: 0x800736B3)>ERROR DETAILS>Following errors were detected during this operation.>* [1/28/2010 10:22:05 AM] System.Runtime.InteropServices.COMException>- The referenced assembly is not installed on your system. (Exception from HRESULT: 0x800736B3)

NOTE: The important part is the COMException. If you don’t see this, then this solution is not applicable.

This means that the Microsoft ClickOnce application store on your computer is corrupted. The solution is as follows:

Go to C:Documents and Settings(your account name)Local Settings.

Rename the “Apps” folder or move it to a different location.

Log in to the Secure Message webapp and start the Secure Messaging Microsoft Office add-in installation.

Note that this solution might affect other ClickOnce programs that you may have installed. To restore a previous state if desired, move the Apps folder to where it was.

2. Based on error reports, it’s possible that a security setting in Internet Explorer has been altered that could be preventing the installation of the add-in. In order to correct it, please follow these instructions:

Open Internet Explorer. Go to Tools > Internet Options. Click the Security tab, and then click on the Custom level button near the bottom. Scroll down until reaching .NET Framework-reliant components. Under this category, look for Run Components Signed with Authenticode, and ensure it is set to Enable.

Try to complete the installation process again. If it fails, please move on to Step 3.

3. There is a possibility that the computer is infected with a virus that is preventing the installation of the add-in. Our investigations have shown that a virus could cause this sort of problem. At this point, if you are still experiencing problems, we recommend consulting your IT department to verify that your computer is virus-free.

Nothing Happens When Clicking Send

The “Outlook Secure Temporary” folder on your computer is full, and Outlook is trying to write to it every time you send a message because you have an image in your signature. This is causing the send failure. This is a known issue with Outlook 2003.

Attachment Size Exceeds Allowable Limit

Even though Secure Messaging allows for attachment file size transfers of up to 5 GB, sometimes Outlook can still restrict users from inserting or selecting large file attachments while composing a secure message.* This is especially true if you are in a corporate setting using Exchange or Outlook 2010 (limited to 20 MB per message). There are two ways to correct the situation:

Contact your administrator to inquire if the asynchronous file attachment feature is enabled on your Secure Messaging account. This feature will allow you to remove this restriction in Outlook. If enabled, you will have the option to “Attach a File” directly from the Delivery Slip, bypassing the Outlook restrictions for the sender and recipients. Using this feature will allow you to send file attachment sizes of up to 5 GB, depending on the configuration of your Secure Messaging platform

For messages that you want to send with large file attachments, use the Secure Messaging webapp.

* This setting only restricts attaching of large files to messages using the native Outlook file attachment picker. Recipients of your messages will be able to view or download any large attachments, regardless of their Exchange or Outlook configurations.

I Use Other Add-ins for MS Outlook (Plaxo, Xobni, etc.)

We are constantly testing with the latest versions of popular add-ins. The record holder is currently 54 concurrent add-ins in Outlook. If you do find an Outlook add-in that appears to be conflicting with the proper functioning of the Secure Messaging add-in, do not hesitate to contact us using the “Report an Error” feature on the Secure Messaging toolbar tab.

What Happens to My Secure Messages if I Uninstall the Secure Messaging Add-in?

If you uninstall the Secure Messaging Outlook add-in, all retrieved and decrypted secure messages are converted into basic email messages. If you have not retrieved a secure message, you will not be able to access it through Outlook after the add-in is uninstalled. You still have the option to access the un-retrieved message from the Secure Messaging webapp. And of course, you are always welcome to reinstall the add-in and retrieve any secure messages you may have overlooked. Re-installing the add-in will also “revive” all your secure messages back into their original condition, including access to the Delivery Slip information.

Does the Add-in Store any Sensitive Data Locally?

The add-in stores some access data locally on your computer. This encrypted cached data consists of information retrieved about secure messages. It is used by the add-in for two primary reasons:

To support offline mode. Without cached information, secure messages would display incorrectly in offline mode.

To make loading of secure messages more efficient. Even when the client is not working in offline mode, it is inefficient to retrieve static data every time a message is selected. The encrypted local cache takes a portion of the load off the server database.

The data that is stored in your local environment is non-sensitive and encrypted regardless. The cache is reported as invalid if it has been tampered with in any way.

How Can I Forward Multiple Messages?

For security reasons, and to protect the integrity of your secure message content, specific bulk forwarding options in Outlook are intentionally disabled by the add-in. However, you can still forward multiple messages by following the quick and easy steps below:

For Outlook 2003 & 2007:

Select the messages you want to forward as you normally would.

Right click, and select “Forward Items.”

For Outlook 2010:

Select the messages you want to forward as you normally would.

Under the “Home” tab in Outlook, select the More drop-down (to the right of the Forward button).

Then, select Forward as attachment. A compose window will appear with your multiple messages as attachments, which you can then send.

Can I Reply to or Forward a Basic Email Message Securely?

Any email message you receive can be changed to a secure message at any time. Simply reply to or forward the basic email message as usual, and then go to the Delivery Slip at the right-hand side of the compose window. If the Delivery Slip is collapsed, click the arrow to expand it. Click on Click here to change delivery options near the top of the Delivery Slip.

Your basic email message is now converted to a secure message. Complete your message and click send. The recipient will now receive the email as a secure message. Alternatively, for Outlook 2007 & 2010 users, simply reply to or forward as usual, and use the Send Secure button instead of the usual Send button. Doing so will send your reply or forward message securely automatically.

Activation Security Confirmation

If the Secure Messaging Outlook add-in is requesting an activation security confirmation, it is because it has detected that Outlook is in “CachedDisconnected” mode with your Exchange server. The add-in requires that Outlook connect to your Exchange directory in “ConnectedFull” mode in order to retrieve your SMTP email address for security and authentication purposes. Without this verification, it could be possible for an intruder to compromise your privacy and security. The add-in will force Outlook to connect with Exchange, which could take up to several minutes.

Note: You must be connected to your Exchange server in order to complete this activation process. If you are unsure if you are connected to Exchange, please contact your administrator.

Note: During this period, Outlook may appear to be non-responsive, but is in fact working. Please wait for the process to complete.

During this time, Outlook may report a “Connected” status with Exchange at the bottom right of the Outlook interface. This is only partially correct, as Outlook is connected to the Exchange mail server, but many components, such as the directory and address book, may not be connected. To view a complete connections status, hold CTRL and right-click on the Outlook icon in the task bar, and select Connection Status.

If the add-in is unable to force Outlook to connect to your Exchange server, another prompt will appear with the following options:

Try Again:
With this option, the add-in uses an alternate method to attempt to initiate “CachedConnectedFull” mode between Outlook and your Exchange server.

Note: While attempting this action, Outlook may appear to be non-responsive, but it is in fact working.

Request Assistance:

If the “Try Again” process fails, please use the “Request Assistance” feature, which will begin the Assisted Activation process. After it is initiated, you will receive a confirmation message in your Outlook inbox within 6 business hours. If you do not receive this message within 6 hours, you may click on the message and re-send the Assistance Request. When you open the confirmation message, you will be able to complete the activation process and begin using the add-in.

Error: Activation SMTP Conversion

If you see this error message, the add-in has detected that Outlook is in “CachedDisconnected” mode with your Exchange server. The add-in requires that Outlook connect to your Exchange directory in “CachedConnectedFull” mode in order to resolve the SMTP email address of the recipient(s) from the Exchange IDs stored in Outlook.

Note: You must be connected to your Exchange server in order to complete this activation process. If you are unsure if you are connected to Exchange, please contact your administrator.

It may look like there is a valid SMTP address in the TO, CC or BCC fields, but for security reasons Outlook does not allow COM add-ins such as the Secure Messaging add-in to access this information. It is necessary, therefore, for the add-in to have Outlook contact your Exchange server to resolve the SMTP address from the Exchange ID.

This process may take some time to complete, and while working, Outlook may appear to be unresponsive. It is in fact working and exchanging information with your Exchange server. Once the correct data is retrieved, the message will be automatically sent. Furthermore, the SMTP address of this recipient will be stored by the add-in, allowing you to skip this step when sending secure messages to this contact in the future.

In Windows XP:

Manual Add-in Installation

Use these simple steps for manually installing the add-in when an antivirus or other program is blocking a regular installation. Please follow these steps in order:

WARNING: Do not skip steps as this could have an adverse effect on your computer.

NOTE: You must confirm that you have Microsoft .NET Framework 4.0 installed on your computer. The add-in requires the .NET Framework to operate.

Navigate to the following Registry Path: HKEY_LOCAL_MACHINESOFTWARE\Microsoft\NET Framework Setup\NDP Confirm that this folder contains a folder with v2.0, and confirm that the string value called “version” under this folder lists the full version number. If the .NET Framework 4.0 is installed, skip to Step 3. If the .NET Framework 4.0 is not installed, proceed to Step 2.

Forward a Specific Message to Support

Sometimes, in order to complete our investigation, we need to take a closer look at the secure message causing the problem. Please follow the steps below in order to send us the specific message. (Try to send it as a secure message attachment, if possible.)

Select the secure message we have requested or that is causing you trouble.

Go to the File menu in Outlook and select Save As.

Name the file anything you want, but make sure you select the option “Outlook Message Format (*.msg)” in the “Save as type” field (by default, the selected type is “HTML (*.htm, *.html)”).

Save it to a location you can remember, e.g. your Desktop.

Start a new secure message in Outlook and attach the file you just saved. Send it to our support department.